Formamide → Oxazole, 4,5-bis(4-methylphenyl)-

HRID 377314Notes

Reaction equation

HRID 377314 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[OH:11])=O)=[CH:4][CH:3]=1.[CH:19]([NH2:21])=O.P(Cl)(Cl)(Cl)=O>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:21]=[CH:19][O:11][C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 24813Phosphorus oxychlorideHCID 2248484,4'-DIMETHYLBENZOIN

Product 1

HCID 19358483Oxazole, 4,5-bis(4-methylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4'-Dimethylbenzoin (25.0 g), formamide (230 ml) and phosphorus oxychloride (16.0 ml) was mixed and stirred under reflux for 5.5 hours. The reaction mixture was cooled to room temperature and poured into water, and then extracted with diethyl ether twice. The collected organic phases were washed with brine and dried over magnesium sulfate and activated carbon. The mixture was filtered and evaporated in vacuo, and then purified by column chromatography on silica. The solvent was evaporated to afford 4,5-bis(4-methylphenyl)oxazole (15.41 g) as a solid.

Workup

  1. temperatureunder reflux for 5.5 hours
  2. extractionextracted with diethyl ether twice
  3. washThe collected organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate and activated carbon
  5. filtrationThe mixture was filtered
  6. customevaporated in vacuo
  7. custompurified by column chromatography on silica
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c3e5c273f8ad4474a69c0e5e8605a4df
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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